This is less gonewildstory than a gone wild custom. I wonder if anyone else has this impression. In my single days, whenever I was going to get lucky to the point of having intercourse with a woman (which admittedly I didn’t do as often as I might have been able to), I would always want to first lick her pussy. Not too original, I know, but in addition to creating some lubrication, I always saw it as a necessary step in the whole ceremony of sex. Specifically, I used to think of the vagina as a door, and I thought, ‘you have to show this door that’s going to allow your penis to enter you appreciate it by kissing and licking her lips and clit. Kinda weird, I’m sure, but wondering if anyone else thought this way. Maybe females even think something along the lines, ‘If I’m going to let him shove his cock in me, he better be licking my pussy fist’? I don’t know – just wanted to see if this was ‘a thing.’
Author: AOLGeneration
[M]y post-nut clarity with [F] from AOL.
As my username makes clear, I was majorly into AOL as a means to meet women in the late ’90’s-early 2000’s. In 2002, when I moved into my first apartment in Chicago after college, I went on a mad terror. I started out doing the somewhat safe thing and meeting women at public places (like Denny’s) before mutually deciding to have them back to my place or go to theirs. But by ’02, I was giving my address to women, and I lived in a doorman building so the doorman would see who I was having up to my apartment at 1 in the morning before I would!
On one such occasion I chatted with a younger gal from the suburbs. She was 18 or 19. She agreed to take the train to the city and come straight to my apartment. She was not bad looking but she seemed kind of slow cognitively, and she had a scar along her temple where she had some sort of brain surgery. She did not tell me this in our chats, but once she arrived since it was so obvious, she mentioned it. She was capable of consent, but it still felt strange. Nonetheless, she came all the way from the suburbs by train to hook up. I felt I owed it to her.
[M]y absolutely blissful evening with over 200 lb. [F]
As you might have guessed from my username, I came of age during the era of AOL. By the time Tinder (or even Craig’s List) came around, I was in a committed relationship with the woman who would eventually become my wife. So in 2000, when this experience took place, the online answer for quick sex or sex play was America Online.
[M]y [F] that got away
My senior year of college I lived alone. Every previous semester, including my study-abroad term, I had roommates. In fact, my freshman year and study abroad semester I actually shared a bedroom with another dude. So finally, I was living completely alone. I had my own bedroom. My own kitchen, den. I could come and go as I pleased and if I were lucky enough to bring a girl back with me, there was never any distractions from a roommate/suitemate or their respective guests. By far I got the most action my senior year, but the funny thing is, as often as I hooked up that year, there were quite a few rejections I’d experienced. It was a numbers game and I tried making a move on every girl I thought I had an opportunity with … every girl except one.
[M]y [F]ortunate Sex Life
***For the sake of anonymity, the names in this account have been altered. All other details are true.***
It was late 2001. I was 24 and enrolled on a series of internet dating sites. I received a message from a woman, Anna, a few years younger than me who had just recently graduated college. She did not have the best profile picture, but I had a pact with myself never to ignore anyone who messaged me. I hated it when I would contact a woman only to be ignored so I couldn’t do it to anyone else. I set up a date, and I was glad I did. Anna looked better in person. She had wide hips and a fairly large ass, but she was also quite tall, so she was athletically proportioned. We had a nice enough date, but there definitely was a disconnect in terms of our loquaciousness. I was always a talky kind of guy; Anna was more on the taciturn side. Still, after dinner she invited me to the apartment into which she had just moved. So new, in fact, that her roommate still hadn’t arrived. We started making out on her couch, and things got pretty intense in a short amount off time. I had two fingers nestled in Anna’s hairy vagina when she asked if I’d like to go into her bedroom. I did, and, again, so new was this apartment that while her mattress had been delivered, she had yet to put sheets and bedding on it. We did not have sex that night, but we did everything but. In fact, with Anna’s upside down pussy on my face, I slid my pinkie finger in her anus. She did not flinch from this and seemed to enjoy it. Anna gave competent head, but my orgasm occurred during a break while she was jerking me off. I distinctly remember cumming on her bare, brand new mattress.
Settle this question between [M]e and my wi[F]e
Admittedly, this is less a story than a question, but there’s enough wildness here to qualify for this sub.
My wife and I have somewhat of a recurring joke. She loves to point out that on our first date nearly 19 years ago, though I tried, she did not let me go down on her. She likes to say that this is the reason we ended up together and that if she gave it up on the first night, the relationship wouldn’t have gone anywhere. I insist that it wouldn’t have made a bit of difference to me and I would have pursued her whether our first date ended in only a kiss, oral, or full-on intercourse.
Fortunately, we enjoy a very open line of communication about sex and our past experiences. So in that spirit, I told her that, while I did not have intercourse with a great number of women before her, it was very common for women I met in college in the mid-nineties – early-2000’s, to let me go down on them and for them to go down on me (or 69) after the first date (or in the case of a bar/party, the same night). My wife responded, “Wow, you met a lot of sluts before me.” I said that I didn’t necessarily think they were promiscuous just because we engaged oral on the first date. Maybe having intercourse on the first date, that I could see as being a little promiscuous, but oral/69-ing struck me as being more tame.
[M]eet-up with a [F]ellow AOL user at the beach and her parents’ house
In the summer of 1999, I was 22 and met Amy, also 22, off of AOL. We went to a diner and then parked at a local beach. Amy had a cute face, auburn hair, and a curvy figure. Not too tall, maybe 5’4, but big tits and wide hips and ass.
We kissed, I popped out her tits and started sucking them. Amy unzips my fly, takes out my erection, starts stroking it. I finger her and discover to my delight a full bush. She’s moaning from my fingering. I start moaning because she’s about to get me off with her amazing hand job. I ejaculate, cum still dripping off my dick, I open the trunk to get a towel I keep back there for times like this when I get lucky.
Next night, we meet again. This time end up at her parents house on the porch swing in back yard. I’m nervous; she’s not. Amy asks if I have condoms. I do. I manage to get one on, but I’m so nervous her parents will catch us that even when this buxom hottie lifts her one piece dress and squats her panty-less hairy vagina on my penis, I lose the erection. NO problem. Amy gives me another awesome hand job, and I shoot jets of semen on her parents’ wooden deck below.
[M]y [f]irst hook-up
If you’ve read my post about ‘Wisconsin women introducing me to the world of sex,’ you know that prior to entering college at the University of Wisconsin, I had never even kissed a girl. I thought I’d detail my first experience with a woman that fateful night in the autumn of 1996 with a Milwaukee gal named Marcie.
This was early in my first semester sophomore year. I had resolved, over the summer, to break my permanent streak of not getting any action. Enter Marcie, a junior from Milwaukee, I met at a local bar my friends and I frequented. Marcie wasn’t beautiful, but she did look like what I could only imagine to be a ‘fun’ girl. Dark, curly hair. A fairly curvy body. I remember she wore brown, polyester pants. Fashionable at the time, if you were around in the mid-nineties, but even then I thought they were unbecoming – kind of like a UPS uniform. Still, I got the impression she’d ‘hook up’ with me, so I started paying for her drinks, and sure enough, when I asked if she wanted to come back to my apartment, she said, “Sure.”
[M]y one night stand with a cute [F] I met that night off of AOL
For my Sept. monthly submission I choose to reflect back on a Polish gal I met off of AOL 19 years ago when I was 25. Her name started with an ‘I,’ and perhaps it’s ubiquitous in Poland, but in case it is as unique as I thought at the time, I will just call her ‘Iris,’ to protect her anonymity.
It’s only my opinion, but I think a good one-night-stand story should meet four criteria: (1) It should include intercourse; (2) It should be mutual – both parties should go into the ‘stand’ knowing it’s just a one-nighter; (3) It may seem obvious, but it must truly be one-time-only – any return trip to the fountain disqualifies it; and (4) There must be something unique that happened unlike any other hook-up you’ve ever had.
I [m] did tongue-in-pussy-nose-in-ass with my [f]avorite gal yesterday.
I just had to announce this because – believe it or not – it’s novel for me. I’ve been married to my wife for 13 years and we dated exclusively for several years before marriage. In that time, I never stuck my nose in her asshole, but I did last night.
She’s meticulous about showering before she’ll let me go down on her. It’s funny because I’ve smelled her vagina when she hasn’t showered and she barely registers a scent. Still, she really wants that soapy certainty in both holes, so if it makes her more comfortable I don’t object.
She did her usual routine. While she did not feel like 69-ing, she was willing, at my request, to assume the position with her ass and pussy hovered over my face. I didn’t care that she wasn’t fellating me. The look and taste of her meaty, pink pussy with beautiful natural blond hair all around it (as well as her anus) was joy enough for me. Her pussy and ass smell like the bar of soap she just used in the shower. They both look and smell nothing but clean. So I figure, ‘she’s got nothing to be concerned about, I’m going all-in.’